Azo dyestuffs and process of making same



Patented Jan. 31, 1928.

UNITED STATES ATJGUST LEOPOLD LASKA AND ARTHUR ZITSCHEB, OF OFFENBACH-ON-THE-MAIN, GERMANY, ASSIGNORS TO I. G. FARBENINDUSTRIE AKTIENGESELLSCHAFT, OF

FRANKFORT, GERMANY.

AZO DYESTUFFS AND PROCESS OF MAKING SAME.

No Drawing. Application filed September 10, 1925, Serial No. 55,627, and in Germany September 20, 1924.

Our invention relates to new azodyestufi's and a process of making same, said dyestuffs having probably the general formula:

' in which formula R represents the residue of a body of the diphenyl series, which dyestufi's are when d scarlet red to black blue powders, soluble in sulfuric acid to a red to greenish blue solution, yielding on reduction with stannous chloride a monoaminobody of the diphenyl series and an arylid of 1-amino-2-hydro'xy-3-naphthoic acid, which dyestuffs are adapted for the production of valuable color lakes, when mixed with the usual substrata, and dye, when produced on the fiber, the vegetable fiber in scarlet red to black blue shades of an excellent fastness,

N-N-Ri O 0-NH-Aryl,

in which formula R represents the residue of a dichlorinated body of the diphenyl series. If the two chlorine atoms of such amino bodies of the diphenyl series are in following maybe mentioned:

PATENT OFFICE.

para-para position, the dyestuffs obtained therefrom have probably the formula:

in which formula R represents the residue of a. 4.4-dichlorinated body of the diphenyl series.

The aminodiphenylbases are obtainable according to the known processes. Among the derivatives, not described hitherto, the

Amino4.4-dichlorodiphenyl, which is obtained by nitrating 4:.4J-dichlorodiphenyl and reducing the nitro compound thus obtained. It forms from alcohol crystalline feebly yellowish needles, melting at 9596 C. (not corrected).

Amino 3.3'-dimethyl i.4-dichlorodiphenyl, obtained by nitrating 4.4-dichloro-3.3- ditolyl and reducing the nitro compound thus obtained, forming from alcohol crystalline colorless needles, melting at 88 (not corrected.)

4-amino-t' hydroxy-diphenyl, obtained by boiling benzidin, which is diazotized only on the one side, forming from alcohol crystalline colorless leaflets, melting at 273 (not corrected).

As azocomponents all the arylids of 2.3- hydroxy-naphthoic acid may be used, such as c. g. the anilid, toluidids, anisidids, phenetidids, alphaand beta-naphthalid, arylids. substituted by chlorine in the a-rylido resi due, the bis-2.3-hydroxynaphthoyl-arylenediamins and others.

The following examples illustrate the invention.

. E wample 1.

Cotton yarn, well boiled and dried, is impregnated with a solution of 10 gr. of the meta-chloroanilid of 2. -hydroxy-naphthoic acid,

115 c.c. of caustic soda solution of 34? B. an i 20 c. c. of Turkey red oil per liter well wrung out and, without being dri developed in a diazo solution containing 4.1 gr. of 4-amino-4-chlorodiphenyl per liter and neutralized with chalk, rinsed and soaped.

In this manner dark garnet red shades of a very good fastness to kier boiling are obtained. The dyestuif thus produced probably has the following formula:

Example 2.

no ClQHN-O c 0 cm Ewample 3.

no Q-HN-OO UH:

Amino-3.3 dimethyllxt dichlorodiphenyl, dyed in the same manner upon the anilid of 2.3-hydroxynaphthoic acid, yields an intense red.

The following table gives the shades of a number of dyeings, prepared according to the present process.

Diazocompound Combined with 2.3-hydroxy- Shade:

ol: naphthoyl- 2-amin0diphenyL- Anllin Bluish red. Do Alpha-naphthylamin Do.

...- Ortho-toluidin Claret red. 4-chl0ro-2-anisidin.... Red. 4-chloro-3-toluidin Scarlet.

.. 3-cl1loro-4-phenetidln Blulsb red Bls-2j+hydroxynaphthoyl- Dark garnet dlanisidin. red. Beta-naphthylamln Claret red Para-toluldin Blulsh red Hhloro-2-anlsldin Do.

2chloro4-anisidln..- Claret red Do 3-chloro-4-toluidln ed. 4-amino-4-chloro- Beta-naphtbylamln.-- Claret red diphenyl.

Do 4chloro-2-anisidin D0. 5-chlero-2-anisidln D0. .1. .S-chloro-Z-toluidln Dari; garnet re Bis-2.3-hydroxynaphthoyl- Brownish gardlanisldin. net red. Amino-4,4-dichlo- Meta-nitroanllin Blulsh red.

rodiphenyl(melting at (lo-96).

Do Alpha-naphthylamin Red.

Para-anisidln Blulsh red. Para-phenetldln Do. Ortho-chloroanilln Scarlet. Do Para-chloroanilln Blulsh red. Amino-3.3'-di- Meta-nltroanilin Claret red.

methyl-4.4-dlchlorodiphenyl.

Do Beta-naphthylamln Intense red. 4-amiuo-4-hydro- Beta-naphthylamln Reddlsh blue.

xydiphenyl.

Do Meta-ehloroanilln Do. Dent Mhloro-2-anlsidln Do.

N ow what we claim is: 1. As new compounds azodyestuffs, having probably the general formula:

in which formula R represents the residue of a body of the diphenyl series, which dyestufis are when dry, scarlet red to black blue powders soluble in sulfuric acid to a red to greenish blue solution, yielding on reduction with stannous chloride a mono amino-. body of the diphenyl series and an arylid of l-aniino-2-hydroxy-3-naphthoic acid, which dyestuffs are adapted for the production of yalu'able color lakes, when mixed with the usual substrate, and, dye, when produced on the fiber the vegetable fiber in scarlet red to black blue shades of an excellent fastness, especially to kier boiling.

2. A process of making new azod estutfs consisting in combining diazotize mono aminobodies of the diphenyl series with the arylids of 2.3-hydroxynaphthoic acid.

3. Materials dyed with the new dyestuffs of claim 1, said dyestufis being produced on the fiber of the material.

4. As new compounds azodyestufi's, having probably the general formula:

in which formula R represents the residue of a dichlorinated body of the diphenyl series, which dyestuffs are when dry scarlet red to dark garnet red powders soluble in sulfuric acid to a red to violet solution, yielding on reduction with stannous chloride a dichlorinated mono aminobody of the diphenyl series and an arylid of l-amino- 2-hydroxy-3-naphthoic acid, which dyestufis are adapted for the production of valuable color lakes, when mixed with the usual substrata, and dye, when produced on the fiber, the vegetable fiber in scarlet red to dark garnet red shades of an excellent fastness, especially to kier boiling.

5. A process of making new azodyestups ich consisting in combining diazotized d rinated mono aminobodies of the diphenyl series with the arylids of 2.3-hydroxynaph thoic acid.

6. Materials dyed with the new dyestufis of claim 4, said dyestufis being produced on the fiber of the material.

7. As new compounds azodyestufis, having probably the general formula:

O-NH-Aryl,

valuablecolor la es, when mixed with the usual substrate, and dye, when produced on the fiber, the vegetable fiber in scarlet red to dark garnet red shades of an excellent fastness, especially to kier boiling.

8. A process of making new azodyestufis consisting in combining diazotized 4.4'-di-- chlorinated mono-aminobodies of the diphenyl series with the 'arylids of 2.3-hydroxynaphthoic acid,

9. Materials dyed with the new dyestufls of claim 7.

In testimony, that we claim the foregoing as our invention, we have signed our names, this 31st da of August 1925.

AUCZUST LEOPOLD LASKA, ARTHUR ZITSCHER. 

